3-Isopropoxy-4-methoxybenzaldehyde → HCID 9863181, compound

HRID 1067380Notes

Reaction equation

HRID 1067380 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH:8]=O)([CH3:3])[CH3:2].[N:15]1([C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([NH2:27])[CH:21]=2)[CH:19]=[N:18][CH:17]=[N:16]1>[N+](C1C=CC=CC=1)([O-])=O>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:8]2[NH:27][C:22]3[CH:21]=[C:20]([N:15]4[CH:19]=[N:18][CH:17]=[N:16]4)[CH:25]=[CH:24][C:23]=3[N:26]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5920923-Isopropoxy-4-methoxybenzaldehydeHCID 10397291HCID 10397291, compound

Product 1

HCID 9863181HCID 9863181, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
150 °C

Procedure

A 5.98 g portion of a known compound 3-isopropoxy-4-methoxybenzaldehyde was added to 4.49 g of 4-(1,2,4-triazol-1-yl)-o-phenylenediamine obtained in Reference Example 2, and the mixture was stirred for 18 hours in 37 ml of nitrobenzene while heating at 150° C. After cooling, nitrobenzene was evaporated under a reduced pressure. By crystallizing the resulting residue with ethyl acetate/hexane, 4.90 g (55%) of the title compound was obtained. Its physical property values are shown as the Compound No. 1 in Table 1.

Workup

  1. customobtained in Reference Example 2
  2. temperatureAfter cooling
  3. customnitrobenzene was evaporated under a reduced pressure
  4. customBy crystallizing the resulting residue with ethyl acetate/hexane

Sources & evidence

ORD record
ord-0f4f5ad32a374f70b335b0e4db6d689a
Source dataset
uspto-grants-2001_06
Patent number
US06248768B1

Reaction notes

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